Today’s #Thursdate is from one of my readers in Boston… and it’s pretty impressive. The date lasted only one drink, and this guy managed to pack in more problems than most guys display over the course of multiple dates.

Pre-Date

The two connected through Coffee Meets Bagel. Although he seemed a bit pretentious based on some of his profile responses and his pictures were a bit blurry, they still scheduled a date to meet after work at a bar. And to properly set the scene, it was a decently nice bar in the Financial District where apparently pretty much everyone shows up in suits or at least some form of business casual clothing.

Problem #1: WTF Are You Wearing

Boston girl arrived at the bar, which was full of professionally dressed men and women. A few minutes after she got situated, Boston Hater came waltzing in wearing baggy mesh shorts, a t-shirt, knee-high socks, basketball shoes, and disheveled hair. It looked like he had just come from the gym or a re-creation of Aaron Carter’s “That’s How I Beat Shaq” video…but he hadn’t. So either this guy is the perfect example of why Queer Eye for the Straight Guy needs to be back on the air, or he was planning to go workout right after the date = he has no patience or respect for his date. All in all, things were headed downhill before they even greeted each other.

Considering this guy’s profile pictures were blurry, I can only imagine how unenthused Boston Girl was to get a close-up of him after having the misfortune of seeing his outfit. The good news is that he wasn’t horrible looking and that the fuzzy images he provided weren’t entirely different from how he looked in person. Buuuut like most guys online, he lied on his height. Boston Girl was in heels and based on the height he provided, that shouldn’t have been a problem. So when they were finally face-to-face, he lost some major points for being barely eye-to-eye with her.

Problem #3: Judge Judy

The two started talking the usual small talk, which of course includes “where are you from/where did you grow up?” Boston Hater was from Philadelphia (now living in Boston), and Boston Girl was from Boston (born and raised). This smooth talker really nailed it with the things he said next:

“Boston girls are the worst. They think they are so hot.”

“Boston girls all think they are such hot shit.”

“If I’m at a bar, I am always trying to be a gentleman, but then I will see a Boston girl across the bar thinking she is all that. So I just go up to girls like that and say, ‘you’re not as hot as you think you are’ and walk away.”

Really strange way to direct the conversation seeing as our gal literally just told him that she was, in fact, a Boston girl (not to mention, who the hell randomly goes up to girls and says something like that?!). It was so bizarre that she interjected shortly after he started his rant and talked about how her family still lives in Boston, how she is still great friends with the girls she grew up with in Boston, how she went to school in Boston. Basically, she wanted to make sure that he she made it clear that the defendant was in the shower she was from Boston and the group of people he was shitting on included the girl sitting next to him at the bar. His response? “Oh, well you’re not one of them.” Ha, great recovery, dickhead.

Problem #4: Pompous

Unlike the depiction of his height in photos, the pretentiousness that shined through on his profile was actually a great indicator for what he was like in person. After he rambled on and on about how he was better than every female in Massachusetts, the conversation shifted to online dating. Boston Hater admitted that this was his first online date…but the only reason for that was because the Coffee Meets Bagel app was broken. Wait, huh? Yep, he explained how Boston Girl was the only match he had gotten so far, which obviously meant that the app wasn’t functioning correctly. Earth to Matilda: it’s not the app.

At that point, she had had enough of this delusional guy and said she had to go once she finished her first drink. She told him “Good luck in Boston!” and expected (and hoped) to never hear from him again. Funny thing is that he actually thought the date went well and he reached out for a second date. NOPE.

Good news, though: Boston Girl did eventually find love through Coffee Meets Bagel! She told me how she and her now-boyfriend were matched through the app and have been together for about a year 🙂 Cheers to love on the East Coast!

This week’s #Thursdate tale is about my mom and her very first online dating experience about two years ago, brought to you by Match.com.

So my mom got matched with this guy, they had some things in common, and she was interested enough to take him up on a date when he asked. They met at a restaurant not too far from where she lived, and he was waiting for her when she arrived. Assuming they would just go sit at the bar for a few drinks and possibly some appetizers, my mom was surprised when her date asked the waitress to be seated at an actual table. Quite frankly, my mom was not too thrilled about this because a) this place was a pretty nice place where the actual entrees were rather heavy and b) every time she had gone there previously, sitting down at a table meant it was going to be an ordeal and stretch the date out longer than she ideally wanted it to be. So my mom braced herself for a less-than-lighthearted dinner date.

The date itself was…meh. My mom explained that this guy looked and acted a lot nerdier, timid, and dull than she had expected. Fortunately, my mom is an outgoing gal that could talk to a wall and somehow manage to make outsiders look like it was a thrilling conversation. (Plus, when she was married to my dad, he was a super quiet guy, and so she was used to filling the silence and leading just about every conversation.) Unfortunately, this is not what she wanted when she agreed to the date – not to mention that she was more interested in him as he appeared and interacted online than in person.

This final part of the date kills me. Dinner ends, they go outside, and they are about to part ways. They exchange quick small talk, my mom thanks him, and is ready to call it a night. But her date asks if he could kiss her. While I am sure there have been instances when asking for a kiss have worked out successfully, I feel like often times it just makes for an awkward experience. Similar to the date, the kiss was…meh. This guy had scruff – and if you keep up with my dating chronicles, then you know that I am a huge fan of scruff, which means I would normally applaud his ability to grow facial hair. But my mom’s date COMPLETELY abused this physical gift he was given by what he said to my mom right after the kiss:

Scruff Abuser: “I am sorry about my scruff.”

My mom: “Oh, um, that’s fine.”

Scruff Abuser: “Well tonight, you can think about feeling it between your thighs.”

WHAT!? I don’t care who you are; it is just not okay to say something like this – especially on a first date. My mom was even more taken aback by this comment because this guy was older, scrawny, nerdy and was so dull during dinner. She basically stood there in shock until they parted ways. Obviously, there was no second date. As for me, it’s great to hear that the dating pool as you get older is clearly so much more mature than what I am exposed to right now.

Since starting this blog, people have begun sharing their dating tales with me. This one in particular stood out to me and ended up inspiring my random #Thursdate blog posts. Why? Because between the many #ThrowbackThursday posts I see on this day, I’ll occasionally come across Instagrammed #Thursdate pics which always depict happy couples on happy dates. Since it’s clear – especially in the single dating world – that dates are not always that successful, this will be somewhat of a “Bad Date Awareness Day.” Enjoy!

The Pre-Date Story
This particular tale comes from College Grad who was fresh out of a long-term relationship. However, the backstory began when she was still in a relationship while school was still in session; that is when she first met the Persistent Sleaze. She was out to dinner with a friend when this random guy invited them to go to a nearby bar (because, you know, beautiful girls over the age of 21 obviously need an invite in order to go to bars that are open to the public). The offer was declined but since he seemed friendly enough, they invited him to the school bars they were heading to. A bit later that night, he met up with College Grad and her friends along with his brother, Persistent Sleaze. Drinking ensued, and Sleaze kept making passes at College Grad despite her continued reminders that she had a boyfriend. Post-bars, Sleaze and bro were not in the best position to drive home, and for some overly gracious reason, College Grad and her friends offered them their couch to crash on. It should’ve been a major warning sign when Sleaze began lurking near her bedroom door to say goodnight, which somehow ended up with him spread eagle on top of her while she was half-asleep in her own bed. They kicked him and his brother out, and that probably should’ve been the last time she saw him.

Flash forward one month, and College Grad was now actually a college grad… and single. Sleaze texted her to invite her to dinner, and despite hesitations, she agreed, and the date was set.

Date #1: …Did He Just Say That?

Persistent Sleaze kicked off the first date with College Grad with the problem of inconvenience. I’m all for being fashionably late, but let’s face it, that luxury is reserved primarily for women – and even then, there is a fine line between what is fashionable and what is rude. For a first date, there is even less leniency with how late is acceptable. So when the Persistent Sleaze was 30 minutes late to pick up College Grad, that’s entering the he-might-be-standing-me-up-and-I-don’t-like-this-one-bit arena. Not only that, but he told her the reason he was late was because he got pulled over for speeding. That’s exactly what every girl wants to hear. “Oh great, not only am I getting into a car with a guy I barely know, but he is also a psycho on the road. Excellent.”

Once they were downtown, the date was going pretty well. There was good conversation, drinks (usually necessary), food (never a bad thing), and College Grad was enjoying herself. After downing a few mojitos, Sleaze was making moves on her and putting his arm around her, but it was all pretty harmless. They continue to have a good time, but a major red flag was raised with a casual comment that he made midway through a normal discussion. “Blah blah blah… I’m really horny.” Wait… what?! It was so random that College Grad brushed it off as him just trying to be funny. Aside from that little derailment, though, the date wasn’t bad. He paid for the bill, drove her home, and kissed her goodnight. Apparently he wasn’t kidding when he said he was horny because it was clear that Sleaze wanted to do a lot more than just kiss. Fortunately, College Grad has a good head on her shoulders and bid him adieu.

Date #2: Used?

After the first date, College Grad had lackluster feelings about seeing Sleaze again. His persistence and overly eager requests to meet up again paid off in his favor, though, because they made plans a second date. He picked her up (more or less on time) and went to a swanky restaurant near his apartment. College Grad was wined and dined on his dime, and she had a genuinely good time. Afterwards, he suggested that they get a bottle of wine and go watch a movie at his apartment nearby. Feeling buzzed from the drinks and confident that she could handle herself, she agreed. They did manage to make it through most of the movie before the makeout sesh started. Things got hot and heavy, and Persistent Sleaze tried to take off her pants. College Grad said no. And this wasn’t a “no but I really mean yes and just don’t want you to think I’m a slut” kind of no – this was a firm NO. Guess what? He kept trying! College Grad stuck her ground, which led to an argument between the two of them. As if that isn’t ridiculous enough, Persistent Sleaze had the audacity to say, “I spent $300 on you. I picked you up in my nice car and took you out to nice places. I don’t like feeling used.”

Clearly, this guy is a total douchebag. Not only had it just been two dates, but this guy thought that he could convince a girl to put out by telling her that her body was worth only $300. (Good luck with that strategy, buddy.) He continued to try to make a case for why she should feel obliged to go beyond her limits and then resorted to accusing her of being dramatic, of using him, and of fucking with his emotions. Persistent Sleaze finally gave up and had to drive her home. Not a single word was uttered throughout the car ride, and he drove away and yelled “SEE YA!” the moment she exited his car. Real nice.

The Aftermath

The very next day, College Grad received a text from Persistent Sleaze apologizing. While it was a genuinely nice message, he was too late and had lost all hope of redemption with her. She ended up sending him a response about how his actions really upset her, and he responded two days later. But he didn’t just respond, he published a novel. She received eight rapid fire texts from him, all of them long paragraphs begging College Grad to meet up again. He tried to convince her that he just wanted to talk and that he’s a good guy – and hey, he very well might be, but all efforts on his end were just pointless now. Her ship had sailed. Adios, motherfucker.